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Search results; Over 1,000 homes in Madison

Top guest favourite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds, 1 private bathroom
25–30 Aug
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4.98 out of 5 average rating, 225 reviews
Top guest favourite
Flat in Church Creek
Nature's Rest in Church Creek
1 bedroom, 1 queen bed
1–6 Aug
4.97 out of 5 average rating, 450 reviews
Top guest favourite
Home in Woolford
Starboard on McKeil Point, w/heated pool & hot tub
6 bedrooms, 11 beds
5–10 Sept
4.99 out of 5 average rating, 142 reviews
Guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds
2–7 Aug
4.96 out of 5 average rating, 99 reviews
Guest favourite
Home in Woolford
Gorgeous Waterfront, Beach, Pool, Pets- 7 Bd /5ba
7 bedrooms, 13 beds
29 Aug – 3 Sept
4.98 out of 5 average rating, 87 reviews
Guest favourite
Room in Cambridge
Sailor's Retreat Pineapple Room
1 bed
11–16 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Church Creek
Blackwater Sika & Wildlife Retreat
3 bedrooms, 4 beds
2–7 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Cambridge
Outline
3 bedrooms, 6 beds
31 Aug – 5 Sept
4.91 out of 5 average rating, 33 reviews
Top guest favourite
Home in Madison
Bayfront Gem w/ Amazing Water Views + Pond!
4 bedrooms, 7 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 59 reviews
Top guest favourite
Room in Cambridge
Farm View Room at Happy Campers
2 single beds
11–16 Aug
4.98 out of 5 average rating, 40 reviews
Guest favourite
Room in Cambridge
Stevens’ Gift, Bay Window with riverview.
2 beds
2–7 Aug
4.96 out of 5 average rating, 46 reviews
Guest favourite
Loft in Cambridge
That 70's Apartment
2 bedrooms, 3 beds
1–6 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Woolford
"Endless Summer" on the Chesapeake!
4 bedrooms, 7 beds
17–22 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
3 bedrooms, 3 beds
11–16 Aug
5.0 out of 5 average rating, 247 reviews
Top guest favourite
Room in Cambridge
Stevens’ Gift, Queen (small room) with river view
1 queen bed
3–8 Aug
4.96 out of 5 average rating, 69 reviews
Home in Cambridge
Family and Pet-Friendly, Waterfront with Pier
4 bedrooms, 5 beds
27 Sept – 2 Oct
Guest favourite
Room in Cambridge
Choptank Charm - 1 bed option
1 king bed
1–6 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Tiny home in Cambridge
The Little House on the Farm, Water Access
1 bedroom, 1 queen bed
8–13 Aug
4.98 out of 5 average rating, 239 reviews
Superhost
Home in Cambridge
Drop Anchor on the Chesapeake
3 bedrooms, 5 beds
1–6 Aug
4.86 out of 5 average rating, 7 reviews